Ever have that “Ugh, I should really reach out to them...” moment?

You want to reconnect, but it feels…awkward. Like, is it random? Too late? Too self-serving?

The good news? It’s never too late to check in with someone you’ve genuinely enjoyed working with—or who already thinks you’re great at what you do. You don’t need a grand reason or perfectly-worded message. You just need to do it.

Let’s break down why reconnection is actually a super smart marketing move, and five low-pressure ways to do it. Plus, we’ll show you how Enji makes the whole thing easier (and a lot less awkward).

• Why reconnection matters (especially for small business owners)
• The 5 ways to reconnect (that don’t feel weird)
• How Enji helps you actually do this
• How to get started

Why Reconnection Matters (Especially for Small Biz Owners)

We’re all about working smarter over here. And that means realizing this key truth:

Warm relationships = the highest-converting leads.

These folks already know you, trust you, and maybe even miss working with you. They’re the ones who:

• Send you referrals
• Write glowing testimonials
• Collaborate on fun projects
• Buy again and again (hello, loyal repeat customers and superfans)

Instead of spending all your energy trying to “find new people,” what if you re-engaged the people who already like you? It takes a lot more time and energy to get in front of a cold lead, show them why you’re trustworthy, and educate them about your products and services. (Read: this is why you feel like marketing is hard.) Meanwhile, your existing relationships could be a treasure trove of new sales. 

Just because someone worked with you once (or chatted in the DMs a few months ago) doesn’t mean the door is closed. And sometimes all it takes is a quick message to remind them you exist—in a good way.

The 5 Ways to Reconnect (That Don’t Feel Weird)

Reaching out doesn’t always feel natural, even if you have a great relationship. We get it—you might feel pesky and annoying. But you’d be surprised how many people are actually happy to receive your message!

1. Send a “Thought of You” DM or Email (Yes, even a meme counts)

Sometimes the best outreach isn’t a sales pitch, it’s a screenshot of something funny or relatable, a podcast you think they’d love, or a “Saw this and thought of your biz!” link.

It can be:

• A “this made me laugh and think of you” message
• A casual check-in: “Hey! How’s everything going with [thing you remember]?”
• A short update that opens the door: “Just wanted to say hi—we just launched a new offer and it made me think of our convo back in [month].”

Low effort, high warmth, and no strings attached is the way to go. 

2. Share Their Work or Refer Them

One of the best ways to show someone you value them? Help other people find them.

Share their post on your stories. Tag them in a thread. Send a friend their way.

People remember the ones who talk about them when they’re not in the room (or the inbox).

By amplifying your customers and colleagues, you’ll build more of a community around your business. People will appreciate your genuine support, rather than just receiving sales messages here and there. 

3. Invite Them to Something

Inviting someone to something casual can help take the pressure off and further your relationship. And it doesn’t have to be an elaborate conference or networking event. 

You can try: 

• A 20-minute virtual coffee chat
• A co-working session
• A “Let’s do a live together!” invite
• A simple “Hey, want to join this webinar I’m attending?”

And if you’re like, “Yeah, but I’ll forget to actually do that,” enter Enji. Pop a recurring task or reminder in your Enji calendar to plan one community touchpoint per month. It takes seconds to set it up the reminder, five minutes to do the follow up, and you’ll thank yourself later.

4. Send a Quick Testimonial or Review

If you’ve ever received a surprise testimonial or thoughtful review, you know how impactful it can be. It builds trust for your business and makes you feel seen.

If you’ve already worked with someone, try leaving a Google review or sending over a few kind words they can use as a testimonial. It takes two minutes. They’ll remember it forever.

Bonus: Screenshot it and share it in your stories while tagging them. Now you’ve helped them with social proof and engagement as well!

5. Respond to Their Stories or Comment on Their Posts

Engagement is hard. Especially when algorithms feel like they’re working against you.

So when you do take the time to respond to someone’s story or leave a thoughtful comment? They notice.

It keeps your name in their orbit and reminds them of how thoughtful and connected you are. (Also, you’re not weird for doing this. Most people love when someone interacts with their content—because it means someone’s actually paying attention!)

How Enji Helps You Actually Do This

You don’t have to keep all your “I should reach out…” thoughts in your head. Enji makes it easy to build reconnection right into your workflow:

• Use the Task Manager to schedule monthly reconnection reminders
• Tap into the “Keep top of mind with past clients” task (it’s already in your Enji system if you have referrals as a channel!)
• Add community-building and check-in touchpoints to your Marketing Calendar
• Track what’s working by keeping an eye on important KPIs, like referral traffic and returning client data, in your KPI Dashboard

And hey, if you want to get fancy? You can even build a simple reconnection workflow in Enji that includes:

• A quarterly task to send 3 check-in emails
• A monthly reminder to comment or engage on 5 client/vendor posts
• A recurring slot on your calendar for “reconnect coffee chats”

We love building a system that makes you look like the most thoughtful person on the internet.

How to Get Started

You don’t need a spreadsheet or CRM overhaul to start reconnecting. Just pick one or two people who’ve been on your mind and send that first message today.

Keep it simple. Keep it real. And let Enji help you stay on top of it going forward.

Not everything has to be a cold pitch or a new campaign. Sometimes, your next best opportunity is already sitting in your inbox, following you on Instagram, or wondering what you’ve been up to lately. Sign into Enji to set up your reminders and then go say hi. 👋

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